Chinese Journal of Organic Chemistry >
A Rapid and Green Synthesis of 8-Aryl-5,7,7-tricyanoisoquinoline Derivatives at Room Temperature under Solvent-Free and Catalyst-Free Conditions
Received date: 2015-12-20
Revised date: 2016-02-25
Online published: 2016-03-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 21571087), and the Brand Major of Universities in Jiangsu Province.
A facile and rapid synthesis of 8-aryl-5,7,7-tricyanoisoquinoline derivatives from the reaction of aromatic aldehydes, malononitrile, and N-substituted-4-piperidones at room temperature under solvent-free and catalyst-free conditions. The N-ethylpiperidin-4-one was first used for the synthesis of 6-amino-2-ethyl-8-aryl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)- tricarbonitrile derivatives. This method offers several advantages in terms of its mild conditions, available raw materials, simple operation, high yields, short reaction time and green process. The products were identified by IR, 1H NMR and HRMS. The reported method is the efficient approach for the synthesis of isoquinoline derivatives.
Gao Yanian , Zhang Mengye , Qian Haiyan , Xie Qianwen , Chen Ming , Xu Shuangshuang , Rong Liangce . A Rapid and Green Synthesis of 8-Aryl-5,7,7-tricyanoisoquinoline Derivatives at Room Temperature under Solvent-Free and Catalyst-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2016 , 36(7) : 1706 -1711 . DOI: 10.6023/cjoc201512025
[1] (a) Bentley, K. W. Nat. Prod. Rep. 2004, 21, 395.
(b) Bentley, K. W. Nat. Prod. Rep. 2006, 23, 444.
(c) Bhadra, K.; Kumar, G. S. Med. Res. Rev. 2011, 31, 821.
[2] Pictet, A.; Gams, A. Ber. Dtsch. Chem. Ges. 1910, 43, 2384.
[3] Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030.
[4] Roy, S.; Roy, S.; Neuenswander, B.; Hill, D. Larock, R. C. J. Comb. Chem. 2009, 11, 1061.
[5] Shi, Z.; Koester, D. C.; Boultadakis-Arapinis, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 12204.
[6] Villuendas, P.; Urriolabeitia, E. P. J. Org. Chem. 2013, 78, 5254.
[7] (a) Niu, Y. N.; Yan, Z. Y.; Gao, G. L.; Wang, H. L.; Shu, X. Z.; Ji, K. G.; Liang, Y. M. J. Org. Chem. 2009, 74, 2893.
(b) Ohta, Y.; Kubota, Y.; Watabe, T.; Chiba, H.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2009, 74, 6299.
(c) Zhang, Z. W.; Lin, A.; Yang, J. J. Org. Chem. 2014, 79, 704.
(d) Chuang, S. C.; Gandeepan, P.; Cheng, C. H. Org. Lett. 2013, 15, 5750.
[8] Rong, L. C.; Han, H. X.; Jiang, H.; Zhuang, Q. Y.; Wang, S. H.; Tu, S. J. Chin. J. Org. Chem. 2009, 29, 962 (in Chinese). (荣良策, 韩红霞, 蒋红, 庄启亚, 王苏惠, 屠书江, 有机化学, 2009, 29, 962.)
[9] Wang, X. S.; Wu, J. R.; Li, Q.; Zhang, M. M.; J. Heterocycl. Chem. 2009, 46, 1355.
[10] Cui, S. L.; Lin, X. F.; Wang, Y. G. J. Org. Chem. 2005, 70, 2866.
[11] Rong, L. C.; Han, H. X.; Jiang, H.; Tu, S. J. Synth. Commun. 2008, 38, 3530.
[12] Victory, P.; Alvarez-Larena, A.; Germain, G.; Kessels, R.; Piniella, J. F.; VidaI-Ferran, A. Tetrahedron 1995, 51, 235.
/
| 〈 |
|
〉 |
